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Pushing your Style Boundaries - What is your most adventurous outfit?

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  • smitty
    replied
    I have a pair of light pink jeans that I wear in the summer. I typically combine it with a navy polo and white minimal sneakers.

    I also love floral pattern shirts. Grand Frank and John Henric sell some of my favorites. Here are a couple of examples:
    https://johnhenric.com/us/shirts/shirt-ulysses
    https://www.grandfrank.com/world/ant...ton-down-shirt

    I also have this shirt:
    https://johnhenric.com/us/shirts/shirt-octavian

    I typically wear these shirts as shown, with dark slacks or dark wash denim. You would be surprised how many people tell me these love these shirts when I wear them. So long as the rest of the outfit it toned down it can look really nice.

    I also wear these shirts under crew neck sweaters. My wife always loves that look.

    Leave a comment:


  • garryowen47
    replied
    Excellent question!

    My style is generally conservative (dark, solid colors, in classic pieces), but I do have a couple items that I indulge with to peacock.

    One of my favorite items is this corduroy shearling collar trucker jacket from Mango Man
    https://shop.mango.com/mn/men/jacket..._33027627.html

    I'm also a big fan of fair isle sweaters and ugly Cosby sweaters. I have this patchwork sweater from Brooks Brothers:
    https://www.pinterest.com/pin/348606827402632323/

    I've been eyeing this sweater from Isabel Marant but it's way outside my budget and now its sold out anyways:
    https://www.isabelmarant.com/us/isab...4009937sv.html

    When the rest of the outfit is understated, it can be easy to naturally incorporate a statement piece into your outfit.

    I also think age matters a lot, too. I'm 31, so I can get away with that shearing jacket for now; but I will probably have to retire it another five to ten years.

    Leave a comment:


  • mark4
    replied
    My most adventurous jacket is a Brooks Brothers Multi-Windowpane check Harris Tweed sportcoat that I got here via swap and shop for cheap. It's loud but not super loud.

    Leave a comment:


  • Arête
    replied
    Originally posted by drchak View Post
    Are you comfortable in a overcoat in a warmish place? I do like the way an overcoat stands out.
    Only like one week out of the year :-p I'm looking to move to a colder climate.

    Leave a comment:


  • hockeysc23
    replied
    Originally posted by drchak View Post
    I dont think of it as attracting comments - more of a diverse look by dressing a bit different. I never understood why 95% winter jackets are grey, black or close to it. So i avoid black or grey suit/coat/shoes.
    Maybe not you but I’d guess the majority that would push style boundaries is to get noticed. That’s why they push them. One upping others etc. doesn’t bother me if ppl prefer that. It’s just not my thing.

    Leave a comment:


  • tayloreuph
    replied
    The double breasted grey and blue windowpane suits aren’t a big stretch for me, they look good, and I wear them well.

    However...

    I do have a couple others.

    The leopard print suit is more of a stretch than the purple one. Maybe more a burgundy than a true purple. The leopard fit off the rack, so obviously I needed to have it. The burgundy needed some tailoring but it also looks slick. I don’t have enough places to wear it, but damn, it’s slick.

    Now, the American Flag shorts romper is just waiting for the right 4th of July party with enough cocktails to make its debut. Or maybe not


    Sent from my iPhone using Tapatalk

    Leave a comment:


  • ryn
    replied
    A silk scarf as a day cravat

    Leave a comment:


  • Ron
    replied
    A pair of red/burgundy corduroys.

    Not very adventurous for most but I'm on the conservative side. Most of my wardrobe is blue, black, grey or white.

    Leave a comment:


  • drchak
    replied


    This has been a big influence on me - an older man dressing this well! From the Italian movie - The Great Beauty.

    Leave a comment:


  • drchak
    replied
    Originally posted by stuffedsuperdud View Post
    I'm a giant attention whore in the summer. It all started when I got a blue and white seersucker suit from Bonobos for basically free. I've never worn the whole suit, as you can't put enough mint juleps into me for me to like this was anything but a costume, but the jacket goes great with white or pastel trousers, a white shirt, linen tie, and white bucks or canvas sneakers. The pants I typically wear with a polo or henley and loafers.

    I also have a tropical worsted teal glen plaid suit that even has an oxymoronic vest. I like wearing hte jacket with white jeans, and a a light blue small print shirt. The pants, again I like with polos and loafers. I occasionally wear the three piece suit with a blue shirt and ancient madder tie, though this is definitely a statement look.

    The only thing I have that is bold to the point of uselessness: A double breasted jacket in bright red Baird McNutt Irish linen. Mildly structured shoulders, butterfly lined in baby blue Bemberg, white MoP buttons, oversized peak lapels with extra belly, and a 6x1 configuration. Not the boxy 1990s 6x1, mind mind you, but a much more obnoxious kind where the 6 buttons are in a big V formation. I typicall wear this with white gabardine pants, loafers, white shirt, no tie. And only to events where I know everyone else will be drunk.
    Damn - this is what i call adventurous! Photos?

    Leave a comment:


  • drchak
    replied
    Originally posted by LesserBlackDog View Post
    I used to have a number of fairly loud jackets including a classic white and blue stripe seersucker jacket, a burgundy wool jacket, an emerald green wool jacket, and an eggplant purple velvet jacket. I wore them all relatively routinely (not frequently, but more than sporadically). None of them fit anymore, unfortunately.

    Just yesterday I got my first ever double breasted jacket (see: WIWT thread) in a bright-ish cobalt herringbone which is the loudest item I've acquired in a while. I was hesitant on the DB style at first but I've warmed up to it quite a bit.

    I sometimes get into jewelry-wearing phases, which I guess is somewhat adventurous by some people's standards. I'm not really in one right now, though I do wear a couple pendant necklaces with casual stuff on occasion. I tend to cycle through ring phases and earring phases mostly.

    I've worn white or off-white pants previously but don't currently have any since my last pair no longer fits.
    Accessories are a great way to stand out - though not brave enough to wear pendant necklaces I experimented with pocket squares and now on the lookout for a thin scarf to rock the Keanu look in "Always be my Maybe" movie (Netflix - very funny).

    Leave a comment:


  • stuffedsuperdud
    replied
    I'm a giant attention whore in the summer. It all started when I got a blue and white seersucker suit from Bonobos for basically free. I've never worn the whole suit, as you can't put enough mint juleps into me for me to like this was anything but a costume, but the jacket goes great with white or pastel trousers, a white shirt, linen tie, and white bucks or canvas sneakers. The pants I typically wear with a polo or henley and loafers.

    I also have a tropical worsted teal glen plaid suit that even has an oxymoronic vest. I like wearing hte jacket with white jeans, and a a light blue small print shirt. The pants, again I like with polos and loafers. I occasionally wear the three piece suit with a blue shirt and ancient madder tie, though this is definitely a statement look.

    The only thing I have that is bold to the point of uselessness: A double breasted jacket in bright red Baird McNutt Irish linen. Mildly structured shoulders, butterfly lined in baby blue Bemberg, white MoP buttons, oversized peak lapels with extra belly, and a 6x1 configuration. Not the boxy 1990s 6x1, mind mind you, but a much more obnoxious kind popularized by Cifonelli, where the 6 buttons are in a big V formation. I typically wear this with white gabardine pants, loafers, white shirt, no tie. And only to events where I know everyone else will be drunk.

    Leave a comment:


  • drchak
    replied
    Originally posted by hockeysc23 View Post
    I think most adventurous to me is a burgundy suit. I’ve always wanted one and finally pulled the trigger. It will only see minimal use but I loved it.

    Pushing style boundaries is not my thing. I’d rather keep a simple classic dappered wardrobe. I don’t need compliments or people going out of their way to notice my outfit. Not against it. Just not my think. My goal coming here was to up my presentation in a business setting but i don’t feel the need to go outside boundaries a lot.

    I’m also in my mid thirties and with a kid. I’m just trying to look up from the dads in bad jeans or joggers and hoodies everywhere.
    I dont think of it as attracting comments - more of a diverse look by dressing a bit different. I never understood why 95% winter jackets are grey, black or close to it. So i avoid black or grey suit/coat/shoes.

    Leave a comment:


  • drchak
    replied
    Are you comfortable in a overcoat in a warmish place? I do like the way an overcoat stands out.

    Leave a comment:


  • LesserBlackDog
    replied
    I used to have a number of fairly loud jackets including a classic white and blue stripe seersucker jacket, a burgundy wool jacket, an emerald green wool jacket, and an eggplant purple velvet jacket. I wore them all relatively routinely (not frequently, but more than sporadically). None of them fit anymore, unfortunately.

    Just yesterday I got my first ever double breasted jacket (see: WIWT thread) in a bright-ish cobalt herringbone which is the loudest item I've acquired in a while. I was hesitant on the DB style at first but I've warmed up to it quite a bit.

    I sometimes get into jewelry-wearing phases, which I guess is somewhat adventurous by some people's standards. I'm not really in one right now, though I do wear a couple pendant necklaces with casual stuff on occasion. I tend to cycle through ring phases and earring phases mostly.

    I've worn white or off-white pants previously but don't currently have any since my last pair no longer fits.

    Leave a comment:

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